Specific reactivity of the O-(β-d-glucopyranosyl-(1→6)-d-glucopyranose) linkage with acetic anhydride in the presence of trimethylsilyl trifluoromethanesulfonate
✍ Scribed by Pierre Angibeaud; Claude Bosso; Jean-Pierre Utille
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- English
- Weight
- 311 KB
- Volume
- 198
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
acetates were formed in 85-90% yield (p-octaacetates were present among other minor unidentified products). Acetylation of 1 with acetic anhydride-trimethylsilyl triflate, gave in a 1:l ratio, two products (2) which were separated by h.p.1.c. or "flash" chromatography. N.m.r. and mass spectrometry, showed the two products to be two isomeric decaacetates resulting from ring opening of the nonreducing unit. Furthermore, deacetylation by the ZemplCn reaction led to two molecules of D-glucose. In the same manner, treatment of gentiotriose3 (5) gave pentadecaacetate derivatives (6) by double ring opening of the nonreducing units, and ZemplCn deacetylation led to three molecules of D-glucose.